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4-(Methylsulfonyl)benzaldehyde → (Z)-5-methoxy-2-methyl-1-(p-methylsulfonylbenzylidene)-3-indenylacetic acid

HRID 377761
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 377761
C[O-].[Na+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][C:10]([CH3:15])=[C:9]2[CH2:16][C:17]([O:19]C)=[O:18].[CH3:21][S:22]([C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)(=[O:24])=[O:23]>O>[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)/[C:11](=[CH:29]\[C:28]1[CH:31]=[CH:32][C:25]([S:22]([CH3:21])(=[O:24])=[O:23])=[CH:26][CH:27]=1)/[C:10]([CH3:15])=[C:9]2[CH2:16][C:17]([OH:19])=[O:18]
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Komponenten

5

Edukt 3

HCID 2203764-(Methylsulfonyl)benzaldehydeHCID 10942334Sodium MethoxideHCID 53634864Methyl 5-methoxy-2-methyl-3-indenylacetate

Produkt 1

HCID 70286603(Z)-5-methoxy-2-methyl-1-(p-methylsulfonylbenzylidene)-3-indenylacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

25% methanolic sodium methoxide (16 ml, 2.0 equivalents) is treated with a solution of methyl 5-methoxy-2-methyl-3-indenylacetate (from Example 4, Part C) (8.7 g; 0.037 mol) and p-methylsulfonylbenzaldehyde, (6.3 g; 1.1 equivalent). The mixture is stirred at reflux under nitrogen for 2 hours. An equal volume of water is added slowly, and refluxing is continued for 30 min. The solution is cooled, is diluted with water and is washed with ether. Residual ether is blown off with nitrogen. The aqueous solution is acidified with 10% hydrochloric acid. The precipitated product is collected and is washed thoroughly with water. The crude product is crystallized from methanol to give (Z)-5-methoxy-2-methyl-1-(p-methylsulfonylbenzylidene)-3-indenylacetic acid.

Aufarbeitung

  1. temperatureat reflux under nitrogen for 2 hours
  2. temperaturerefluxing
  3. temperatureThe solution is cooled
  4. washis washed with ether
  5. customThe precipitated product is collected
  6. washis washed thoroughly with water
  7. customThe crude product is crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-113586e271734fa8a1342d6dff985c0c
Quelldatensatz
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06028116

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